NP-MRD: Showing NP-Card for Tetrahydroberberine (NP0137494)

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Record Information

Version

2.0

Created at

2022-05-30 16:54:06 UTC

Updated at

2026-02-22 04:01:11 UTC

NP-MRD ID

NP0137494

Natural Product DOI

https://doi.org/10.57994/7947

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Tetrahydroberberine

Description

Canadine, also known as xanthopuccine, belongs to the class of organic compounds known as protoberberine alkaloids and derivatives. These are alkaloids with a structure based on a protoberberine moiety, which consists of a 5,6-dihydrodibenzene moiety fused to a quinolizinium and forming 5,6-Dihydrodibenzo(a,g)quinolizinium skeleton. Tetrahydroberberine is found in Argemone mexicana, Berberis cretica, Berberis heteropoda, Corydalis ambigua, Corydalis cava, Corydalis intermedia, Corydalis ophiocarpa, Corydalis solida, Corydalis turtschaninovii, Corydalis yanhusuo, Coscinium fenestratum, Glaucium arabicum, Glaucium squamigerum, Hydrastis canadensis, Lindera glauca, Macleaya cordata, Magnolia compressa, Annona mucosa, Sanguinaria canadensis and Zanthoxylum ailanthoides. Tetrahydroberberine was first documented in 2013 (PMID: 23747414). Canadine is a strong basic compound (based on its pKa) (PMID: 24324259) (PMID: 25093987).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161520062D          

 25 29  0  0  0  0            999 V2000
    2.2354   -0.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6370   -0.7999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4619   -0.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8635   -1.5331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6884   -1.5457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1117   -0.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9366   -0.8501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3600   -0.1420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9584    0.5787    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3817    1.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2066    1.2743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6082    0.5536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4331    0.5410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8347   -0.1796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6389   -0.3634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7127   -1.1851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9540   -1.5092    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4113   -0.8877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5864   -0.8752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1849   -0.1545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1335    0.5912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7101   -0.1169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8852   -0.1043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4837    0.6163    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6587    0.6289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 14 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
  8 20  1  0  0  0  0
 12 20  1  0  0  0  0
  9 21  1  0  0  0  0
 21 22  1  0  0  0  0
  6 22  1  0  0  0  0
 22 23  2  0  0  0  0
  3 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
M  END

     RDKit          3D

 46 50  0  0  0  0  0  0  0  0999 V2000
   -6.2224    1.5314   -0.1212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3134    0.4782   -0.2706 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9613    0.5828   -0.0015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4399    1.7760    0.4426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0883    1.9077    0.7195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2430    0.8381    0.5526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7430   -0.3695    0.1081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1030   -0.4797   -0.1640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6234   -1.6750   -0.6085 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7236   -2.0268   -1.9579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9230   -1.5703   -0.1021 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4724   -1.4102    0.1442 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8842   -1.8878    1.4275 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3621   -1.8348    1.6054 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0277   -0.8370    0.7292 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4282   -0.7783    0.7765 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1135    0.1227   -0.0089 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4056    0.9807   -0.8557 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0054    0.9075   -0.8896 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3321    0.0069   -0.1037 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8645   -0.0626   -0.1465 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2253    0.9116    0.8319 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3519    1.7580   -1.5073 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4858    1.7814   -0.6367 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4782    0.4216   -0.1868 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7602    2.4290   -0.6035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4073    1.7294    0.9391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1810    1.3600   -0.6327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1133    2.6351    0.5780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6928    2.8500    1.0674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3231   -1.2470   -2.6389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7951   -2.1475   -2.2036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2462   -3.0136   -2.1726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3284   -2.3827    0.5439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0394   -1.8560   -1.1848 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3270   -1.3593    2.2564 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5061   -2.9496    1.5034 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6179   -1.6440    2.6886 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7818   -2.8624    1.4011 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0017   -1.4258    1.4184 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5194    1.5962   -1.5641 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4467    0.1947   -1.1429 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3745    0.6427    1.8773 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6355    1.9073    0.6164 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2217    2.4217    0.2114 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4016    2.0494   -1.1630 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6 22  1  0
 22 21  1  0
 21 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 23  1  0
 23 24  1  0
 24 25  1  0
 18 19  1  0
 19 20  2  0
 12 11  1  0
 11  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  8  3  1  0
  7  6  1  0
 20 21  1  0
 20 15  1  0
 25 17  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  5 30  1  0
 22 43  1  0
 22 44  1  0
 21 42  1  6
 13 36  1  0
 13 37  1  0
 14 38  1  0
 14 39  1  0
 16 40  1  0
 24 45  1  0
 24 46  1  0
 19 41  1  0
 11 34  1  0
 11 35  1  0
 10 31  1  0
 10 32  1  0
 10 33  1  0
M  END


  Mrv1533004161520062D          

 25 29  0  0  0  0            999 V2000
    2.2354   -0.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6370   -0.7999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4619   -0.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8635   -1.5331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6884   -1.5457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1117   -0.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9366   -0.8501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3600   -0.1420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9584    0.5787    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3817    1.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2066    1.2743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6082    0.5536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4331    0.5410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8347   -0.1796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6389   -0.3634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7127   -1.1851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9540   -1.5092    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4113   -0.8877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5864   -0.8752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1849   -0.1545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1335    0.5912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7101   -0.1169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8852   -0.1043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4837    0.6163    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6587    0.6289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 14 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
  8 20  1  0  0  0  0
 12 20  1  0  0  0  0
  9 21  1  0  0  0  0
 21 22  1  0  0  0  0
  6 22  1  0  0  0  0
 22 23  2  0  0  0  0
  3 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0137494

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C2CC3N(CCC4=CC5=C(OCO5)C=C34)CC2=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C20H21NO4/c1-22-17-4-3-12-7-16-14-9-19-18(24-11-25-19)8-13(14)5-6-21(16)10-15(12)20(17)23-2/h3-4,8-9,16H,5-7,10-11H2,1-2H3

> <INCHI_KEY>
VZTUIEROBZXUFA-UHFFFAOYSA-N

> <FORMULA>
C20H21NO4

> <MOLECULAR_WEIGHT>
339.391

> <EXACT_MASS>
339.14705816

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
37.72145803107781

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
16,17-dimethoxy-5,7-dioxa-13-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁵,²⁰]henicosa-2,4(8),9,15,17,19-hexaene

> <ALOGPS_LOGP>
2.70

> <JCHEM_LOGP>
3.0865507193333337

> <ALOGPS_LOGS>
-3.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
4.902648773833444

> <JCHEM_POLAR_SURFACE_AREA>
40.160000000000004

> <JCHEM_REFRACTIVITY>
94.196

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.98e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
canadin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0       4.173  -0.148   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.922  -1.493   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       6.462  -1.517   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.212  -2.862   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.752  -2.885   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.542  -1.563   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.082  -1.587   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.872  -0.265   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      11.122   1.080   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      11.912   2.402   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.452   2.379   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      14.202   1.033   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      15.742   1.010   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      16.491  -0.335   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      17.993  -0.678   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      18.130  -2.212   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      16.714  -2.817   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      15.701  -1.657   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      14.161  -1.634   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.412  -0.288   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.582   1.104   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.792  -0.218   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.252  -0.195   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       6.503   1.150   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       4.963   1.174   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   23                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   22                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   20                                                  
CONECT    9    8   10   21                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   20                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   18                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   14   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19    8   12                                                  
CONECT   21    9   22                                                       
CONECT   22   21    6   23                                                  
CONECT   23   22    3   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   58    0
END

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Synonyms

Value	Source
5,8,13,13a-Tetrahydro-9,10-dimethoxy-6H-benzo(g)-1,3-benzodioxolo(5,6-a)quinolizine	ChEBI
5,8,13,13a-Tetrahydro-9,10-dimethoxy-6H-benzo(g)benzo-1,3-dioxolo(5,6-a)quinolizine	ChEBI
9,10-Dimethoxy-2,3-(methylenedioxy)berbine	ChEBI
Canadin	ChEBI
Tetrahydroberberine	ChEBI
Xanthopuccine	ChEBI
Canadine, (+-)-isomer	MeSH
Canadine, (R)-isomer	MeSH
Canadine hydrochloride	MeSH
Canadine, (S)-isomer	MeSH

Chemical Formula

C₂₀H₂₁NO₄

Average Mass

339.3910 Da

Monoisotopic Mass

339.14706 Da

IUPAC Name

16,17-dimethoxy-5,7-dioxa-13-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁵,²⁰]henicosa-2,4(8),9,15,17,19-hexaene

Traditional Name

canadin

CAS Registry Number

Not Available

SMILES

COC1=CC=C2CC3N(CCC4=CC5=C(OCO5)C=C34)CC2=C1OC

InChI Identifier

InChI=1S/C20H21NO4/c1-22-17-4-3-12-7-16-14-9-19-18(24-11-25-19)8-13(14)5-6-21(16)10-15(12)20(17)23-2/h3-4,8-9,16H,5-7,10-11H2,1-2H3

InChI Key

VZTUIEROBZXUFA-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Argemone mexicana	LOTUS Database	35616633
Berberis cretica	LOTUS Database	35616633
Berberis heteropoda	LOTUS Database	35616633
Corydalis ambigua	LOTUS Database	35616633
Corydalis cava	LOTUS Database	35616633
Corydalis intermedia	LOTUS Database	35616633
Corydalis ophiocarpa	LOTUS Database	35616633
Corydalis solida	LOTUS Database	35616633
Corydalis turtschaninovii	LOTUS Database	35616633
Corydalis yanhusuo	LOTUS Database	35616633
Coscinium fenestratum	LOTUS Database	35616633
Glaucium arabicum	LOTUS Database	35616633
Glaucium squamigerum	LOTUS Database	35616633
Hydrastis canadensis	LOTUS Database	35616633
Lindera glauca	LOTUS Database	35616633
Macleaya cordata	LOTUS Database	35616633
Michelia compressa	LOTUS Database	35616633
Rollinia mucosa	LOTUS Database	35616633
Sanguinaria canadensis	LOTUS Database	35616633
Sphenocentrum jollyanum		Not Available
Zanthoxylum ailanthoides	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as protoberberine alkaloids and derivatives. These are alkaloids with a structure based on a protoberberine moiety, which consists of a 5,6-dihydrodibenzene moiety fused to a quinolizinium and forming 5,6-Dihydrodibenzo(a,g)quinolizinium skeleton.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Protoberberine alkaloids and derivatives

Sub Class

Not Available

Direct Parent

Protoberberine alkaloids and derivatives

Alternative Parents

Substituents

Protoberberine skeleton
Tetrahydroprotoberberine skeleton
Tetrahydroisoquinoline
Benzodioxole
Anisole
Alkyl aryl ether
Aralkylamine
Benzenoid
Tertiary aliphatic amine
Tertiary amine
Organoheterocyclic compound
Oxacycle
Ether
Acetal
Azacycle
Hydrocarbon derivative
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

aromatic ether (CHEBI:22998 )
organic heteropentacyclic compound (CHEBI:22998 )
berberine alkaloid (CHEBI:22998 )
oxacycle (CHEBI:22998 )
a small molecule (S-TETRAHYDROBERBERINE )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.7	ALOGPS
logP	3.09	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Basic)	4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	40.16 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	94.2 m³·mol⁻¹	ChemAxon
Polarizability	37.72 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Canadine

METLIN ID

Not Available

PubChem Compound

34458

PDB ID

Not Available

ChEBI ID

22998

Good Scents ID

Not Available

References

General References

Chen S, Wan L, Couch L, Lin H, Li Y, Dobrovolsky VN, Mei N, Guo L: Mechanism study of goldenseal-associated DNA damage. Toxicol Lett. 2013 Jul 31;221(1):64-72. doi: 10.1016/j.toxlet.2013.05.641. Epub 2013 Jun 5. [PubMed:23747414 ]
Dang TT, Facchini PJ: CYP82Y1 is N-methylcanadine 1-hydroxylase, a key noscapine biosynthetic enzyme in opium poppy. J Biol Chem. 2014 Jan 24;289(4):2013-26. doi: 10.1074/jbc.M113.505099. Epub 2013 Dec 9. [PubMed:24324259 ]
Wu H, Waldbauer K, Tang L, Xie L, McKinnon R, Zehl M, Yang H, Xu H, Kopp B: Influence of vinegar and wine processing on the alkaloid content and composition of the traditional Chinese medicine Corydalis Rhizoma (Yanhusuo). Molecules. 2014 Aug 4;19(8):11487-504. doi: 10.3390/molecules190811487. [PubMed:25093987 ]
DOI: 10.3987/com-89-5168

Showing NP-Card for Tetrahydroberberine (NP0137494)

MOL for NP0137494 (Tetrahydroberberine)

3D MOL for NP0137494 (Tetrahydroberberine)

3D SDF for NP0137494 (Tetrahydroberberine)

3D-SDF for NP0137494 (Tetrahydroberberine)

PDB for NP0137494 (Tetrahydroberberine)

3D PDB for NP0137494 (Tetrahydroberberine)

SMILES for NP0137494 (Tetrahydroberberine)

INCHI for NP0137494 (Tetrahydroberberine)

Structure for NP0137494 (Tetrahydroberberine)

3D Structure for NP0137494 (Tetrahydroberberine)